Earn point on your loyalty program!arrow arc left

Cheap flights from Boston (BOS) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Boston to Chicago in April , May 2026

25 Apr - 13 May $ 245.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates
11 Apr - 06 May $ 692.00
BOS
Boston
Spirit Airlines
2 STOPS
CHI
Chicago
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
Pick dates
10 Apr - 05 May $ 1,067.00
BOS
Boston
Spirit Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Spirit Airlines
1 STOPS
BOS
Boston
Pick dates

Last minute flights from Boston to Chicago

28 Apr - 30 Apr $ 252.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates
09 Apr - 30 Apr $ 281.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates
13 Apr - 30 Apr $ 281.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates

One-way flights to Chicago from Boston

12:30 PM - 12:30 PM
United Airlines
0 Stops
2h 59m
BOS - CHI
$ 84
Kiwi
Pick dates
8:15 AM - 8:15 AM
United Airlines
0 Stops
2h 57m
BOS - CHI
$ 113
Kiwi
Pick dates
8:15 AM - 8:15 AM
United Airlines
0 Stops
2h 57m
BOS - CHI
$ 113
Kiwi
Pick dates

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.